Synthesis of 1-deoxysphingosine derivatives with conformationally restricted pyrrolidinediol head groups.

Autor: Dougherty AM; Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA., McDonald FE, Liotta DC, Moody SJ, Pallas DC, Pack CD, Merrill AH
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2006 Feb 16; Vol. 8 (4), pp. 649-52.
DOI: 10.1021/ol052839v
Abstrakt: [structure: see text] A family of cyclic 1-deoxysphingolipid derivatives of structure 4 has been designed and synthesized, which may serve as tumorigenesis suppressors for various cancers. Compound 4 is a second-generation analogue developed from sphingosine (1), in which a hydroxyl substituent is moved from C1 to C5 and a methylene is added for conformational rigidity between the C2-nitrogen substituent and C4. The synthetic chemistry for pyrrolidine ring closure at C3-C4 features ring-closing metathesis followed by hydroboration-oxidation.
Databáze: MEDLINE